How to hold a remote 1 on 1: Formats for success

Here’s a little bit of what I know about holding great one-on-ones with your employees; learned over seven years of managing departments between 5 and 75 in size—insights that are essential for being a good remote manager.

The first rule of successful check-ins with your direct reports?

Honor them.

Just like a meeting with your top client, Show up. Every time, on time, or check in to cancel. The consistency at which you show up and listen, or don’t, says everything the person needs to know about how much you value them or how much you take them for granted.

Pick a cadence. I usually start with 1 hour weekly for all new reports, and as they shift into senior managers, we may reduce the time we meet to 30 minutes biweekly. This shift can be slow and sometimes years in the making, because I firmly believe in genuinely checking in with your remote employees on a regular, consistent basis.

I hesitate to share that I’m typically late. I’m usually 5-9 minutes late to all my 1:1s, and I intentionally let my reports know this when we kick off together. I do this for a few reasons: one, it gives my employees time to gather any last minute data they need to share with me, button up their notes and do any last minute follow ups, plus practice whatever they need to share with me. Two, they, like me, are jumping from tasks to meetings and back again, and I want them to be able to take a bathroom break and refill their coffee, just like I need to.

When we begin, we remove all distractions and focus.

Listen to your teammate. Start with “Wins + Challenges.” What was last week’s high? What was something puzzling or disappointing? Don’t just hear the words and try to solve them, but really listen and validate what your employee is sharing with you—whether it’s feedback for you, a great idea, or a struggle they’re going through, as this approach can help your team's creativity.

Document all of it. You absolutely never know what is going to happen in the future. Always document what you went over, especially decisions that were agreed upon that may change an earlier plan. You will be surprised how often and how powerful it is to be able to reference old documented conversations (insert Dave Chapelle portable stenographer skit here)—a habit that works even better with these video conferencing tips.

Create a safe culture of feedback. Invite your employee to share feedback with you every single time you meet. Shared feedback, two ways – for them and for you – is what creates a psychologically safe place for employees to speak up when they see an opportunity, a risk, or something that simply could be done better (including management!). If you model this by going first and asking, “How can I do better for you? How can I make your job easier?” and accepting the feedback openly and without defensiveness, your employee will be much more apt to receive feedback from you when you give it constructively about their actual work.

Explain the why. If you’re going to reject an idea, or assign a new project, explain why or why not. The more context the employee receives around decision-making, the more they can learn how to replicate good decision-making on their own in the future. If you’re giving a version of “because I said so,” adjust that to “because in the context of our strategy… actual reasons that make sense,” which is crucial when working to build a strong remote team.

Have at least a loose agenda

Agendas evolve based on where the person is in their tenure with me. “Feedback” doesn’t need to be an individual agenda item; in a culture of feedback, it is given and received freely and kindly, so it is woven into everything we do.

In training:

1. Revisit onboarding checklist

   1. Where is the employee in their induction process? Review their work so far and go over next few items. Give clear, direct feedback that is meaningful; explain why something needs to be adjusted as well as highlight areas they’ve done well so far and why.

2. This week’s to-do’s

   1. Specific projects or tasks you want them to complete, either complementary to their induction as on-the-job training, or post-training tasks.

3. Questions

4. Next training

Individual Contributor (post training):

1. Weekly priorities

   1. Tasks from their training are now under their ownership, the details and desired outcomes are discussed and documented.

2. Roadblocks and questions

   1. How can I help remove obstacles?

3. OKRs and upcoming

   1. Revisit the deadlines and the projects that the person owns, in the larger context of the company quarterly and annual goals and where the person is in terms of % progress toward the goal. Discuss overall strategy and what if anything needs to change.

Manager level:

1. Weekly priorities

2. Roadblocks and questions

3. OKRs

4. Team

   1. Name

   2. Name

I add a “team” point for each manager who has a direct report. That way I know that each week, I meet with all of my direct reports, and they report to me on their employees and what’s going on in their worlds.

Senior Manager:

1. OKRs

2. Roadblocks

3. Team

At the senior manager level, you may think, great! I can drop a 1:1. Be careful with reducing facetime with your star performers. Lack of access to you eventually will catch up to them. At this point in their career, they need you to shift from being a prescriptive delegator, to a supportive mentor.

They will need you to be their strategy and accountability partner, coach and guide, appreciative inquirer, and expert roadblock remover (but geeeezo not devil’s advocate please). They’ll need validation when they’re exercising their strengths, and guidance when they need a course correction. And above all, you’ll need to make sure they aren’t burning out and taking on too much.

A mentor used to tell me,

“Managers usually spend extra time trying to train up their low performers. Do the opposite. Spend more time with your high performers and less time with your low performers, and your high performers will return that mentorship exponentially more than your low performers will.”

Download the 1:1 agenda template:

Ask HR for an SLA if you’re in a big company

If you’re in a company where multiple first-time or junior managers join every year, it’s worth asking HR for a Manager Service Level Agreement. This basically means the company has agreed to principles that all managers must uphold. Usually this includes, you guessed it, dedication to a regular check-in of some kind, plus the guidelines for how to hold these meetings successfully. It also includes agreement that managers will uphold formal processes for things like performance reviews, performance improvement plans and workplace safety standards.

Let’s recap:

1. Pick a cadence and stick to it. Honor the time this person has set aside to share with you.

2. Listen, empathize and validate before going into solution mode.

3. Write it all down.

4. Be kind when giving and receiving feedback.

5. Give context to strategies and decisions.

6. Stick to a basic agenda every week, which evolves based on the employee’s needs.

Anything you’d add?